Hexakis{4-[(4 -hydroxybiphenyl-4-yl)ethynyl]phenyl}benzene
|
|
- Charla Lynn Barker
- 6 years ago
- Views:
Transcription
1 Molbank 2015, M865; doi: /m865 Short Note OPEN ACCESS molbank ISSN Hexakis{4-[(4 -hydroxybiphenyl-4-yl)ethynyl]phenyl}benzene Silvia Valera and Bela E. Bode * EaStCHEM School of Chemistry, Biomedical Sciences Research Complex and Centre of Magnetic Resonance, University of St Andrews, KY16 9ST Fife, UK; sv22@st-andrews.ac.uk * Author to whom correspondence should be addressed; beb2@st-andrews.ac.uk; Tel.: ; Fax: Academic Editor: Norbert Haider Received: 13 May 2015 / Accepted: 24 June 2015 / Published: 2 July 2015 Abstract: A novel polyphenolic backbone, hexakis{4-[(4 -hydroxybiphenyl-4- yl)ethynyl]phenyl}benzene, was synthesised using a common synthetic protocol used for the synthesis of similar polyphenolic compounds. Keywords: hexaphenylbenzene; phenol Introduction Pulsed Electron Paramagnetic Resonance (EPR) [1,2] techniques have become powerful tools for elucidation of structure and conformational flexibility of complex biological systems [3], such as photosynthetic reaction centres [4], integral membrane proteins [5] and nucleic acids [6]. Pulsed EPR measurements give access to accurate distance measurements of 1.2 to 8 nm between two or more paramagnetic centres, which can be endogenous or chemically introduced by Site-Direct Spin Labelling (SDSL) [3]. Distance measurements in systems containing two spin labels have been proven to be easily accessible and highly accurate and precise [3], however, in multiply labelled complexes these measurements have been proven challenging because of the presence of multi-spin effects. These effects can introduce artefacts hampering data interpretation [7,8]. To quantify and suppress multi-spin effects in pulsed EPR measurements multiply labelled chemical model systems have been synthesised [7,9]. These give access to a better understanding of the phenomenon as they allow measurements to be performed on well-defined systems and under well-defined experimental conditions. Model systems are often much easier to simulate.
2 Molbank 2015 M865 (Page 2) Results and Discussion As a precursor to a novel six-fold labelled multi-spin model systems the intermediate hexaphenol hexakis{4-[(4 -hydroxybiphenyl-4-yl)ethynyl]phenyl}benzene has been isolated. The synthetic process, reported in Scheme 1, involved the iodination of hexaphenylbenzene [10] using a similar protocol designed by Kobayashi et al. [11], followed by Sonogashira cross-coupling, under conditions previously reported by Mohamed Ahmed and Mori [12], and optimised for synthesis of similar polyphenols [9]. Scheme 1. Synthesis of hexaphenol hexakis{4-[(4 -hydroxybiphenyl-4-yl)ethynyl]phenyl}benzene 2. Experimental Section General Methods Sonogashira cross-couplings were carried out under nitrogen atmosphere using standard Schlenk techniques and freshly distilled solvents. Dry solvents were obtained anhydrous by a SPS alumina column and collected into flame-dried flasks. Solvents for cross-couplings were degassed via the freeze-pump-thaw technique ( 3). 1 H and 13 C{ 1 H} NMR experiments (Bruker Avance 500, Fällanden, Switzerland) were performed using a 300 or 500 MHz 1 H 125 MHz 13 C at ambient temperature in deuterated solvents. Infrared spectra were recorded with an ATR probe and only characteristics peaks are reported (Shimadzu, Kyoto, Japan). Mass spectrometry data was acquired using matrix-assisted laser desorption/ionisation (MALDI) (Voyager DE-STR, Applied Biosystems, Foster City, CA, USA). Hexakis{4-[(4 -hydroxybiphenyl-4-yl)ethynyl]phenyl}benzene (2) Hexakis(4-iodophenyl)benzene (1) was prepared in modified literature procedures [11]. Hexaphenylbenzene (2 g, 3.7 mmol) was dissolved in dry CH2CL2 (150 ml). To the obtained solution freshly ground iodine (3.8 g, 15 mmol) was added together with [bis-(trifluoroaceteoxy)iodo] benzene (6.4 g, 15 mmol); 3.2 g was added just after addition of iodine and the remaining half was added after
3 Molbank 2015 M865 (Page 3) 30 min. The obtained mixture was left stirring in the dark under nitrogen atmosphere overnight. Hexane was added to the yellow solution to encourage precipitation. The solids were isolated by filtration. The obtained solids were dissolved in chloroform; the solution was washed with 5% sodium bisulfite aqueous solution followed by water and brine. The organic layer was dried over sodium sulfate and solvents removed under reduced pressure. The obtained solids were recrystallized from chloroform to give 1 as a white solid (0.35 g, 51 %) [11,13]. Hexakis(4-iodophenyl)benzene (0.1 g, 0.08 mmol) was dissolved in dry THF (10 ml) together with PdCl2(PPh3)2 (6% mol., g, mmol). 4ʹ-Ethynyl-[1,1ʹ-biphenyl]-4-ol (0.12 g, 0.62 mmol) was dissolved in a separate flask in dry THF (10 ml). Both solutions were degassed before drop-wise addition of the alkyne solution to the first solution. The new mixture was degassed once more before addition of CuI (12%, 0.01 g, 0.08 mmol). A 0.5 M aqueous ammonia solution (2.5 ml, 1.3 mmol) was added drop-wise to the new mixture, which was left stirring at 65 C for 4 days. The mixture was taken up in EtOAc and washed with 10% aqueous HCl solution, water and brine. The organic phase was dried over sodium sulfate and solvents removed under vacuum. The obtained solids (0.2 g) were purified via silica column chromatography (10% EtOAc in CH2CL2, Rf 0.1). The target molecule was isolated as a brown solid (0.07 g, 55%). FT-IR (ATR): 2916 (m), 2848 (m), 1662 (m), 1589 (m), 1492 (m), 1274 (m), 1172 (m), 1047 (s), 1022 (s), 997 (s), 821 (s). 1 H NMR (500 MHz, DMSO-d6) δ 9.66 (s, 6H), 7.56 (dd, J = 37.2, 7.2 Hz, 36H), 7.18 (d, J = 7.9 Hz, 12H), 7.01 (d, J = 8.0 Hz, 12H), 6.84 (d, J = 8.3 Hz, 12H). 13 C NMR (126 MHz, DMSO) δ , , , , , , , , , , , , , 89.81, MS [MALDI] [M + H] + calcd for C126H78O , found H and 13 C NMR spectra are reported in the supplementary materials as Figures S1 and S2 together with MALDI mass spectra as Figures S3 to S5. Acknowledgments We acknowledge Melanja Smith and Tomas Lebl for NMR experiments, the EPSRC UK National Mass Spectrometry Service Centre at Swansea University and the BSRC Mass Spectrometry and Proteomics Facility, St Andrews. SV is supported by the EPSRC, UK; BEB is grateful for an EaStCHEM Hirst Academic Fellowship by the School of Chemistry, St Andrews and funding from the People Programme (Marie Curie Actions) of the European Union s Seventh Framework Programme (REA ). There are no competing financial interests. Author Contributions SV and BEB planned the research, SV performed the research and analysed the data, SV and BEB wrote the paper.
4 Molbank 2015 M865 (Page 4) Conflicts of Interest The authors declare no conflict of interest. References 1. Milov, A.D.; Salikhov, K.M.; Shirov, M.D. Application of the double resonance method to electron spin echo in a study of the spatial distribution of paramagnetic centres in solids. Sov. Phys. Solid State 1981, 23, Pannier, M.; Veit, S.; Godt, A.; Jeschke, G.; Spiess, H.W. Dead-time free measurement of dipole dipole interactions between electron spins. J. Magn. Reson. 2000, 142, Jeschke, G. DEER distance measurements on proteins. Annu. Rev. Phys. Chem. 2012, 63, Shigemori, K.; Hara, H.; Kawamori, A.; Akabori, K. Determination of distances from tyrosine D to QA and chlorophyllz in photosystem II studied by `2+1' pulsed EPR. BBA-Bioenergetics 1998, 1363, Ward, R.; Pliotas, C.; Branigan, E.; Hacker, C.; Rasmussen, A.; Hagelueken, G.; Booth, I.R.; Miller, S.; Lucocq, J.; Naismith, J.H.; et al. Probing the structure of the mechanosensitive channel of small conductance in lipid bilayers with pulsed electron-electron double resonance. Biophys. J. 2014, 106, Krstić, I.; Endeward, B.; Margraf, D.; Marko, A.; Prisner, T. Structure and dynamics of nucleic acids. In EPR Spectroscopy; Drescher, M., Jeschke, G., Eds.; Springer: Berlin, Germany; Heidelberg, Germany, 2012; Volume 321, pp Jeschke, G.; Sajid, M.; Schulte, M.; Godt, A. Three-spin correlations in double electron-electron resonance. Phys. Chem. Chem. Phys. 2009, 11, Giannoulis, A.; Ward, R.; Branigan, E.; Naismith, J.H.; Bode, B.E. PELDOR in rotationally symmetric homo-oligomers. Mol. Phys. 2013, 111, Valera, S.; Taylor, J.E.; Daniels, D.S.B.; Dawson, D.M.; Athukorala Arachchige, K.S.; Ashbrook, S.E.; Slawin, A.M.Z.; Bode, B.E. A modular approach for the synthesis of nanometer-sized polynitroxide multi-spin systems. J. Org. Chem. 2014, 79, Hyatt, J.A. Synthesis of a hexaalkynylhexaphenylbenzene. Org. Prep. Proced. Int. 1991, 23, Kobayashi, K.; Kobayashi, N.; Ikuta, M.; Therrien, B.; Sakamoto, S.; Yamaguchi, K. Syntheses of hexakis(4-functionalized-phenyl)benzenes and hexakis[4-(4ʹ-functionalizedphenylethynyl)phenyl]benzenes directed to host molecules for guest-inclusion networks. J. Org. Chem. 2005, 70, Mohamed Ahmed, M.S.; Mori, A. Sonogashira coupling with aqueous ammonia directed to the synthesis of azotolane derivatives. Tetrahedron 2004, 60, FT-IR (ATR): 1487 (m), 1138 (m), 1058 (m), 1003 (s), 823 (m). 1 H NMR (300 MHz, Chloroform-d) δ 7.23 (s, 12H), (m, 12H). 14. ESI and EI mass spectrometry methods did not give the wanted ions. Low resolution MALDI techniques gave the wanted mass peak, however high resolution analysis using MALDI could not
5 Molbank 2015 M865 (Page 5) be achieved due to the lack of an appropriate standard. Microanalysis for 2 did not give acceptable results. We attribute this to the hygroscopic nature of the compound. Similar behaviour with respect to microanalysis and mass spectrometry was found for similar compounds bearing several phenol groups (see Ref. 9) by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (
Effect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information (ESI) for Effect of Conjugation and Aromaticity of 3,6 Di-substituted
More informationSupporting Information. Visualization of Phagosomal Hydrogen Peroxide Production by A Novel Fluorescent Probe That Is Localized via SNAP-tag Labeling
Supporting Information Visualization of Phagosomal Hydrogen Peroxide Production by A Novel Fluorescent Probe That Is Localized via SNAP-tag Labeling Masahiro Abo, Reiko Minakami, Kei Miyano, Mako Kamiya,
More informationHow to build and race a fast nanocar Synthesis Information
How to build and race a fast nanocar Synthesis Information Grant Simpson, Victor Garcia-Lopez, Phillip Petemeier, Leonhard Grill*, and James M. Tour*, Department of Physical Chemistry, University of Graz,
More informationSupporting Information. for. Synthetic routes to [Au(NHC)(OH)] (NHC = N- heterocyclic carbene) complexes
Supporting Information for Synthetic routes to [Au(HC)(OH)] (HC = - heterocyclic carbene) complexes Adrián Gómez-Suárez, Rubén S, Alexandra M. Z. Slawin and Steven P. olan* EaStChem School of chemistry,
More informationSupporting Information for
Supporting Information for Deuteration of boranes: catalysed versus non-catalysed processes David J. Nelson, Jonathan B. Egbert and Steven P. Nolan* EaStCHEM, School of Chemistry, University of St. Andrews,
More informationYujuan Zhou, Kecheng Jie and Feihe Huang*
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 A redox-responsive selenium-containing pillar[5]arene-based macrocyclic amphiphile: synthesis,
More informationSupporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S
Supporting Text Synthesis of (2S,3S)-2,3-bis(3-bromophenoxy)butane (3). Under N 2 atmosphere and at room temperature, a mixture of 3-bromophenol (0.746 g, 4.3 mmol) and Cs 2 C 3 (2.81 g, 8.6 mmol) in DMS
More informationSolvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Solvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols
More informationA TTFV pyrene-based copolymer: synthesis, redox properties, and aggregation behaviour
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 A TTFV pyrene-based copolymer: synthesis, redox properties, and aggregation behaviour Eyad
More informationSupporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2002
Supporting Information for Angew. Chem. Int. Ed. Z19663 Wiley-VCH 2002 69451 Weinheim, Germany Selective Measurements of a itroxide-itroxide Distance of 5 nm and a itroxide-copper distance of 2.5 nm in
More informationThe First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C
Supporting Information The First Asymmetric Total Syntheses and Determination of Absolute Configurations of Xestodecalactones B and C Qiren Liang, Jiyong Zhang, Weiguo Quan, Yongquan Sun, Xuegong She*,,
More informationSupporting Information. Vesicles of double hydrophilic pullulan and. poly(acrylamide) block copolymers: A combination
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2017 Supporting Information Vesicles of double hydrophilic pullulan and poly(acrylamide) block
More informationSupporting Information
Supporting Information (Tetrahedron. Lett.) Cavitands with Inwardly and Outwardly Directed Functional Groups Mao Kanaura a, Kouhei Ito a, Michael P. Schramm b, Dariush Ajami c, and Tetsuo Iwasawa a * a
More informationRhodamine B pentyl ester and its methyl, ethyl, propyl, and butyl homologues
Rhodamine B pentyl ester and its methyl, ethyl, propyl, and butyl homologues Author Cosgrove, Kelly Published 2006 Journal Title Molbank Version Published DOI https://doi.org/10.3390/m515 Copyright Statement
More informationTuning Porosity and Activity of Microporous Polymer Network Organocatalysts by Co-Polymerisation
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Tuning Porosity and Activity of Microporous Polymer Network Organocatalysts
More informationSynthesis of Secondary and Tertiary Amine- Containing MOFs: C-N Bond Cleavage during MOF Synthesis
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2015 Supporting Information Synthesis of Secondary and Tertiary Amine- Containing MFs: C-N Bond
More informationPulsed Electron Electron Double Resonance
Pulsed Electron Electron Double Resonance (PELDOR oder DEER) T. F. Prisner Institute of Phys. & Theor. Chemistry Center of Biological Magnetic Resonance Goethe University Frankfurt www.prisner.de Teaching
More informationSupporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A
Fuerst et al. Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A S1 Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers:
More informationEfficient Mono- and Bis-Functionalization of 3,6-Dichloropyridazine using (tmp) 2 Zn 2MgCl 2 2LiCl ** Stefan H. Wunderlich and Paul Knochel*
Efficient Mono- and Bis-Functionalization of 3,6-Dichloropyridazine using (tmp) 2 Zn 2Mg 2 2Li ** Stefan H. Wunderlich and Paul Knochel* Ludwig Maximilians-Universität München, Department Chemie & Biochemie
More informationSupplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4)
Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4) A solution of propenyl magnesium bromide in THF (17.5 mmol) under nitrogen atmosphere was cooled in an ice bath and
More informationSupplementary Material. Ionic liquid iodinating reagent for mild and efficient iodination of. aromatic and heteroaromatic amines and terminal alkynes
Supplementary Material onic liquid iodinating reagent for mild and efficient iodination of aromatic and heteroaromatic amines and terminal alkynes Mahboobe Nouzarian 1, Rahman Hosseinzadeh 1,*, and Hamid
More informationSupporting Information
Supporting Information Wiley-VCH 2009 69451 Weinheim, Germany page S1 Relative orientation of rigid nitroxides by pulsed EPR spectroscopy: Beyond distance measurements in nucleic acids Olav Schiemann 1,2
More informationSupporting Information. Application of the Curtius rearrangement to the synthesis of 1'- aminoferrocene-1-carboxylic acid derivatives
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018 Supporting Information Application
More informationSupplementary Information (Manuscript C005066K)
Supplementary Information (Manuscript C005066K) 1) Experimental procedures and spectroscopic data for compounds 6-12, 16-19 and 21-29 described in the paper are given in the supporting information. 2)
More informationSupplementary Figure 2. Full power on times. Histogram showing on times of bursts with 100 pm 1, 100 pm 2 and 1 nm Et 3 N at full laser power.
S1 Supplementary Figures Supplementary Figure 1. Time-correlated still frame images. Expanded still frames images from TIRFM video of CuAAC of 1 and 2 and corresponding intensity trajectory of a single
More informationSynthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain
rganic Lett. (Supporting Information) 1 Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain Charles Kim, Richard Hoang and Emmanuel A. Theodorakis* Department of Chemistry
More informationA long-lived iridium(iii) chemosensor for the real-time
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B. This journal is The Royal Society of Chemistry 2017 Supporting Information A long-lived iridium(iii) chemosensor for the real-time
More informationSynthesis and Use of QCy7-derived Modular Probes for Detection and. Imaging of Biologically Relevant Analytes. Supplementary Methods
Synthesis and Use of QCy7-derived Modular Probes for Detection and Imaging of Biologically Relevant Analytes Supplementary Methods Orit Redy a, Einat Kisin-Finfer a, Shiran Ferber b Ronit Satchi-Fainaro
More informationSupporting Information. (1S,8aS)-octahydroindolizidin-1-ol.
SI-1 Supporting Information Non-Racemic Bicyclic Lactam Lactones Via Regio- and cis-diastereocontrolled C H insertion. Asymmetric Synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.
More informationSupporting Information for
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017 Supporting Information for
More informationSupporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003
Supporting Information for Angew. Chem. Int. Ed. Z53001 Wiley-VCH 2003 69451 Weinheim, Germany 1 Ordered Self-Assembly and Electronic Behavior of C 60 -Anthrylphenylacetylene Hybrid ** Seok Ho Kang 1,
More informationCarbene) Catalyzed Alcohol Oxidation Using. Molecular Oxygen
Supporting information for [Pd(HC)(PR 3 )] (HC = -Heterocyclic Carbene) Catalyzed Alcohol Oxidation Using Molecular Oxygen Václav Jurčík, Thibault E. Schmid, Quentin Dumont, Alexandra M. Z. Slawin and
More informationSupplementary Information. Mapping the Transmission Function of Single-Molecule Junctions
upplementary Information Mapping the Transmission Function of ingle-molecule Junctions Brian Capozzi 1, Jonathan Z. Low 2, Jianlong Xia 3, Zhen-Fei Liu 4, Jeffrey B. Neaton 5,6, Luis M. Campos 2, Latha
More informationSupplementary Materials: SRG Inscription in Supramolecular Liquid Crystalline Polymer Film: Replacement of Mesogens
Supplementary Materials: SRG Inscription in Supramolecular Liquid Crystalline Polymer Film: Replacement of Mesogens Shun Mitsui, Mitsuo Hara, Shusaku Nagano, and Takahiro Seki S. Synthesis Materials Sodium
More informationAn Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol
An Efficient Total Synthesis and Absolute Configuration Determination of Varitriol Ryan T. Clemens and Michael P. Jennings * Department of Chemistry, University of Alabama, 500 Campus Dr. Tuscaloosa, AL
More informationAntiparallel double-stranded BODIPY porphyrin dyad assembled by a self-complementary B F Zn interaction
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Supporting Information for Antiparallel double-stranded BODIPY porphyrin dyad assembled by a self-complementary
More informationSupplementary Material
10.1071/CH13324_AC CSIRO 2013 Australian Journal of Chemistry 2013, 66(12), 1570-1575 Supplementary Material A Mild and Convenient Synthesis of 1,2,3-Triiodoarenes via Consecutive Iodination/Diazotization/Iodination
More informationAppendix A. Supplementary Information. Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Appendix A Supplementary Information Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized
More informationElectronic Supporting Information
Electronic Supporting Information for the manuscript Tunable Absorption and Emission Wavelength in Conjugated Microporous Polymers by Copolymerization by Jessica Brandt, a Johannes Schmidt, b Arne Thomas,
More informationSignificant improvement of dye-sensitized solar cell. performance by a slim phenothiazine based dyes
Significant improvement of dye-sensitized solar cell performance by a slim phenothiazine based dyes Yong Hua, a Shuai Chang, b Dandan Huang, c Xuan Zhou, a Xunjin Zhu, *a,d Jianzhang Zhao, c Tao Chen,
More informationSupporting information
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 205 A simple and greener approach
More informationSupplementary Information
Supplementary Information C aryl -C alkyl bond formation from Cu(ClO 4 ) 2 -mediated oxidative cross coupling reaction between arenes and alkyllithium reagents through structurally well-defined Ar-Cu(III)
More informationA dual redox-responsive supramolecular amphiphile fabricated by selenium-containing pillar[6]arene-based molecular recognition
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 A dual redox-responsive supramolecular amphiphile fabricated by selenium-containing pillar[6]arene-based
More informationSUPPORTING INFORMATION. Fathi Elwrfalli, Yannick J. Esvan, Craig M. Robertson and Christophe Aïssa
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 SUPPORTING INFORMATION S1 Fathi Elwrfalli, Yannick J. Esvan, Craig M. Robertson and Christophe
More informationSupplementary Information. for. Stable Supramolecular Helical Structure of C 6 -Symmetric
Supplementary Information for Stable Supramolecular Helical Structure of C 6 -Symmetric Hydrogen-Bonded Hexakis(phenylethynyl)benzene Derivatives with Amino Acid Pendant Groups and Their Unique Fluorescence
More informationSupporting Information
Supporting Information Selective Synthesis of [6]-, [8]-, and [10]Cycloparaphenylenes Eiichi Kayahara, 1,2 Takahiro Iwamoto, 1 Toshiyasu Suzuki, 2,3 and Shigeru Yamago* 1,2 1 Institute for Chemical Research,
More informationSupporting Information
Supporting Information Incorporation of a Sugar Unit into a C C N Pincer Pd Complex Using Click Chemistry and Its Dynamic Behavior in Solution and Catalytic Ability toward the Suzuki Miyaura Coupling in
More informationHalogen halogen interactions in diiodo-xylenes
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) for CrystEngComm. This journal is The Royal Society
More informationSupporting Information
Supporting Information Precision Synthesis of Poly(-hexylpyrrole) and its Diblock Copolymer with Poly(p-phenylene) via Catalyst-Transfer Polycondensation Akihiro Yokoyama, Akira Kato, Ryo Miyakoshi, and
More informationSimple Solution-Phase Syntheses of Tetrahalodiboranes(4) and their Labile Dimethylsulfide Adducts
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Supporting Information for: Simple Solution-Phase Syntheses of Tetrahalodiboranes(4) and their
More informationSupporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and
Supporting Information for A rapid and efficient synthetic route to terminal arylacetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3- butyn-2-ols Jie Li and
More informationSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Supporting Information Unmasking Representative Structures of TMP-Active Hauser and Turbo Hauser Bases Pablo García-Álvarez, David V. Graham,
More informationBlock: Synthesis, Aggregation-Induced Emission, Two-Photon. Absorption, Light Refraction, and Explosive Detection
Electronic Supplementary Information (ESI) Luminogenic Materials Constructed from Tetraphenylethene Building Block: Synthesis, Aggregation-Induced Emission, Two-Photon Absorption, Light Refraction, and
More informationElectronic Supporting Information
Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. This journal is the wner Societies 217 Electronic Supporting Information Emergence of polar order and tilt in terephthalate
More informationTrisulfur Radical Anion as the Key Intermediate for the. Synthesis of Thiophene via the Interaction between Elemental.
Trisulfur Radical Anion as the Key Intermediate for the Synthesis of Thiophene via the Interaction between Elemental Sulfur and NaOtBu Guoting Zhang, a Hong Yi, a Hong Chen, a Changliang Bian a Chao Liu
More informationSupporting Information
Efficient Greenish Blue Electrochemiluminescence from Fluorene and Spirobifluorene Derivatives Federico Polo, *,, Fabio Rizzo, *, Manoel Veiga Gutierrez, Luisa De Cola, Silvio Quici Physikalisches Institut,
More informationEnantioselectivity switch in copper-catalyzed conjugate addition. reaction under influence of a chiral N-heterocyclic carbene-silver complex
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supplementary Information Enantioselectivity switch in copper-catalyzed conjugate addition
More informationSupplementary Material. Photostimulated synthesis of 2-(diphenylphosphino)benzoic acid by the S RN 1 reaction
Supplementary Material Photostimulated synthesis of 2-(diphenylphosphino)benzoic acid by the S RN 1 reaction Silvia M. Barolo, Sandra E. Martín,* Roberto A. Rossi* INFIQC, Departamento de Química Orgánica,
More informationA supramolecular approach for fabrication of photo- responsive block-controllable supramolecular polymers
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information A supramolecular approach for fabrication of photo- responsive
More informationAziridine in Polymers: A Strategy to Functionalize Polymers by Ring- Opening Reaction of Aziridine
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information (ESI) Aziridine in Polymers: A Strategy to Functionalize
More informationElectronic Supplementary Information for. A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective
Electronic Supplementary Information for A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective and Sensitive Detection of H 2 S: Synthesis, Spectra and Bioimaging Changyu Zhang, 1 Runyu Wang,
More informationSupplementary Information. Solvent-Dependent Conductance Decay Constants in Single Cluster. Junctions
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2016 Supplementary Information Solvent-Dependent Conductance Decay Constants in Single Cluster
More informationChiral nematic organo-siloxane oligopodes based on an axially chiral binaphthalene core
Chiral nematic organo-siloxane oligopodes based on an axially chiral binaphthalene core Christopher P. J. Schubert, M. Gabriela Tamba and Georg, H. Mehl * Department of Chemistry, University of Hull, Hull,
More informationSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Concise Stereoselective Synthesis of ( )-Podophyllotoxin by Intermolecular Fe III -catalyzed Friedel-Crafts Alkylation Daniel Stadler, Thorsten
More informationSupporting Information
Supporting Information Total Synthesis of (±)-Grandilodine B Chunyu Wang, Zhonglei Wang, Xiaoni Xie, Xiaotong Yao, Guang Li, and Liansuo Zu* School of Pharmaceutical Sciences, Tsinghua University, Beijing,
More informationSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany S1 Stereoselective Synthesis of α,α-chlorofluoro Carbonyl Compounds Leading to the Construction of luorinated Chiral Quaternary Carbon Centers
More informationSupporting Information. for. A two step synthesis of a key unit B precursor of. cryptophycins by asymmetric hydrogenation
Supporting Information for A two step synthesis of a key unit B precursor of cryptophycins by asymmetric hydrogenation Benedikt Sammet, Mathilde Brax and Norbert Sewald* Address: Bielefeld University,
More informationSupporting Information for
Supporting Information for AmPhos Pd-Catalyzed Suzuki-Miyaura Catalyst-Transfer Condensation Polymerization: Narrower Dispersity by Mixing the Catalyst and Base Prior to Polymerization Kentaro Kosaka,
More informationRed Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via Chiral Transfer of the Conjugated
More informationSupporting Information:
Enantioselective Synthesis of (-)-Codeine and (-)-Morphine Barry M. Trost* and Weiping Tang Department of Chemistry, Stanford University, Stanford, CA 94305-5080 1. Aldehyde 7. Supporting Information:
More informationElectronic Supplementary Information. ligands for efficient organic light-emitting diodes (OLEDs)
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 27 Electronic Supplementary Information bis-zn II salphen complexes bearing pyridyl functionalized
More informationSupporting Information
Supporting Information Wiley-VCH 2012 69451 Weinheim, Germany Substitution of Two Fluorine Atoms in a Trifluoromethyl Group: Regioselective Synthesis of 3-Fluoropyrazoles** Kohei Fuchibe, Masaki Takahashi,
More informationFacile Multistep Synthesis of Isotruxene and Isotruxenone
Facile Multistep Synthesis of Isotruxene and Isotruxenone Jye-Shane Yang*, Hsin-Hau Huang, and Shih-Hsun Lin Department of Chemistry, National Taiwan University, Taipei, Taiwan 10617 jsyang@ntu.edu.tw
More informationSupporting Information
Supporting Information Wiley-VCH 2012 69451 Weinheim, Germany Concise Syntheses of Insect Pheromones Using Z-Selective Cross Metathesis** Myles B. Herbert, Vanessa M. Marx, Richard L. Pederson, and Robert
More informationA Photocleavable Linker for the Chemoselective Functionalization of Biomaterials
Electronic Supplementary Information A otocleavable Linker for the Chemoselective Functionalization of Biomaterials Liz Donovan and Paul A. De Bank* Department of armacy and armacology and Centre for Regenerative
More informationStoichiometric Reductions of Alkyl-Substituted Ketones and Aldehydes to Borinic Esters Lauren E. Longobardi, Connie Tang, and Douglas W.
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2014 Supplementary Data for: Stoichiometric Reductions of Alkyl-Substituted Ketones and Aldehydes
More informationMaksim A. Kolosov*, Olesia G. Kulyk, Elena G. Shvets, Valeriy D. Orlov
1 Synthesis of 5-cinnamoyl-3,4-dihydropyrimidine-2(1H)-ones Supplementary Information Maksim A. Kolosov*, lesia G. Kulyk, Elena G. Shvets, Valeriy D. rlov Department of organic chemistry, V.N.Karazin Kharkiv
More informationSupporting Information
Cyclo[4]carbazole, An Iodide Anion Macrocyclic Receptor Huangtianzhi Zhu, a Bingbing Shi, a Kexian Chen, b Peifa Wei, a Danyu Xia, a Julfikar Hassan Mondal, a and Feihe Huang* a a State Key Laboratory
More informationA Sumanene-based Aryne, Sumanyne
A Sumanene-based Aryne, Sumanyne Niti Ngamsomprasert, Yumi Yakiyama, and Hidehiro Sakurai* Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871
More informationBODIPY Based Self-healing Fluorescent Gel Formation via Acylhydrazone Linkage
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 BODIPY Based Self-healing Fluorescent Gel Formation via Acylhydrazone Linkage Tugba Ozdemir
More informationTetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon
SUPPLEMENTARY METHODS Solvents, reagents and synthetic procedures All reactions were carried out under an argon atmosphere unless otherwise specified. Tetrahydrofuran (THF) was distilled from benzophenone
More informationSynthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity
Supporting Information for Synthesis of Glaucogenin D, a Structurally Unique Disecopregnane Steroid with Potential Antiviral Activity Jinghan Gui,* Hailong Tian, and Weisheng Tian* Key Laboratory of Synthetic
More informationSynthesis, characterization and molecular recognition of bis-platinum terpyridine dimer. Supporting information
This journal is (c) The Royal Society of Chemistry 008 Synthesis, characterization and molecular recognition of bis-platinum terpyridine dimer Robert Trokowski, Shigehisa Akine, Tatsuya abeshima Graduate
More informationSupporting Information
Supporting Information SmI 2 -Mediated Carbon-Carbon Bond Fragmentation in α-aminomethyl Malonates Qiongfeng Xu,, Bin Cheng, $, Xinshan Ye,*, and Hongbin Zhai*,,,$ The State Key Laboratory of Natural and
More informationQile Wang, and Nan Zheng* Department of Chemistry and Biochemistry, University of Arkansas. Fayetteville, Arkansas,
Supporting Information A Photocatalyzed Synthesis of Naphthalenes by Using Aniline as a Traceless Directing Group in [4+2] Annulation of AminoBenzocyclobutenes with Alkynes Qile Wang, and Nan Zheng* Department
More informationSupporting Information
Supporting Information Rhodium-Catalyzed Annulation Reactions of 2-Cyanophenylboronic Acid with Alkynes and Strained Alkenes Tomoya Miura and Masahiro Murakami* Department of Synthetic Chemistry and Biological
More informationTriazabicyclodecene: an Effective Isotope. Exchange Catalyst in CDCl 3
Triazabicyclodecene: an Effective Isotope Exchange Catalyst in CDCl 3 Supporting Information Cyrille Sabot, Kanduluru Ananda Kumar, Cyril Antheaume, Charles Mioskowski*, Laboratoire de Synthèse Bio-rganique,
More informationSupporting Information
Supporting Information An Extremely Active and General Catalyst for Suzuki Coupling Reactions of Unreactive Aryl Chlorides Dong-Hwan Lee and Myung-Jong Jin* School of Chemical Science and Engineering,
More informationLight irradiation experiments with coumarin [1]
Materials and instruments All the chemicals were purchased from commercial suppliers and used as received. Thin-layer chromatography (TLC) analysis was carried out on pre-coated silica plates. Column chromatography
More informationSupplementary Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supplementary Information SUPPORTING INFORMATION Novel and selective detection of Tabun mimics
More informationA Novel Polytriazole-based Organogel Formed by the Effects. of Copper Ions
Supporting Information for A Novel Polytriazole-based Organogel Formed by the Effects of Copper Ions Key Laboratory for Specially Functional Polymeric Materials and Related Technology of the Ministry of
More informationSupplementary Figure 1 IR Spectroscopy. 1Cu 1Ni Supplementary Figure 2 UV/Vis Spectroscopy. 1Cu 1Ni
Supplementary Figure 1 IR Spectroscopy. IR spectra of 1Cu and 1Ni as well as of the starting compounds, recorded as KBr-pellets on a Bruker Alpha FTIR spectrometer. Supplementary Figure 2 UV/Vis Spectroscopy.
More informationSupporting Information
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2017 Supporting Information Direct copper-catalyzed oxidative trifluoromethylthiolation
More informationSupporting Information
Supporting Information Organocatalytic Enantioselective Formal Synthesis of Bromopyrrole Alkaloids via Aza-Michael Addition Su-Jeong Lee, Seok-Ho Youn and Chang-Woo Cho* Department of Chemistry, Kyungpook
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Rh 2 (Ac) 4 -Catalyzed 2,3-Migration of -rrocenecarboxyl -Diazocarbonyl
More informationSupporting Information. Rhodium, iridium and nickel complexes with a. 1,3,5-triphenylbenzene tris-mic ligand. Study of
Supporting Information for Rhodium, iridium and nickel complexes with a 1,3,5-triphenylbenzene tris-mic ligand. Study of the electronic properties and catalytic activities Carmen Mejuto 1, Beatriz Royo
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 214 Supporting Information Lei Liu, ab Yijie Xia, b Jie Zhang* b a) China Center for Modernization
More informationSupporting Information
Supporting Information Control the Structure of Zr-Tetracarboxylate Frameworks through Steric Tuning Jiandong Pang,,,,# Shuai Yuan,,# Junsheng Qin, Caiping Liu, Christina Lollar, Mingyan Wu,*, Daqiang
More informationLight-Controlled Switching of a Non- Photoresponsive Molecular Shuttle
Supporting Information Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle Liu-Pan Yang, a,b Fei Jia, a Jie-Shun Cui, a Song-Bo Lu, a and Wei Jiang* a a Department of Chemistry, South
More informationHighly Luminescent -Conjugated Dithienometalloles: Photophysical Properties and Application to Organic Light-Emitting Diodes
Electronic Supplementary Information (ESI) Highly Luminescent -Conjugated Dithienometalloles: Photophysical Properties and Application to Organic Light-Emitting Diodes Ryosuke Kondo, a Takuma Yasuda,*
More information